Hydrochloric Acid → [Rac]-2-[1-methyl-3-oxo-3-phenyl-(z)-propenylamino]-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid

HRID 479176Notes

Reaction equation

HRID 479176 reaction equation
C([O:3][C:4](=[O:43])[CH:5]([NH:31]/[C:32](/[CH3:42])=[CH:33]\[C:34](=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:6][C:7]1[C:12]2[S:13][CH:14]=[CH:15][C:11]=2[C:10]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:42]/[C:32](/[NH:31][CH:5]([CH2:6][C:7]1[C:12]2[S:13][CH:14]=[CH:15][C:11]=2[C:10]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[O:22][C:23]=2[CH3:24])=[CH:9][CH:8]=1)[C:4]([OH:43])=[O:3])=[CH:33]/[C:34](=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69557618[Rac]-2-[1-methyl-3-oxo-3-phenyl-(z)-propenylamino]-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid ethyl ester

Product 1

HCID 69557841[Rac]-2-[1-methyl-3-oxo-3-phenyl-(z)-propenylamino]-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acidYield 69%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.333 g (0.56 mmol) [rac]-2-[1-Methyl-3-oxo-3-phenyl-(Z)-propenylamino]-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid ethyl ester were dissolved in THF/EtOH 1:1 (10 ml) and treated with 1.4 ml (1.4 mmol) aqueous sodium hydroxide solution (1 molar) and the reaction mixture was stirred for 1 hour at room temperature. It was then acidified with 1N hydrochloric acid and extracted with dichloromethane. The combined organic phases were dried over MgSO4 and evaporated. Purification by flash-chromatography (silica gel, eluent: gradient of dichloromethane and methanol) gave 0.218 g (69%) [rac]-2-[1-methyl-3-oxo-3-phenyl-(Z)-propenylamino]-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid as light yellow amorphous solid.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customevaporated
  4. customPurification by flash-chromatography (silica gel, eluent: gradient of dichloromethane and methanol)

Sources & evidence

ORD record
ord-dfb27eb1069e4abca9103090f06600ba
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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